Photo By Amy Hall
Tip to Tip Tour

The Five-Forty

This 540 km (336 mi) route packs in more gravel and more climbing as you cross the Island on gravel roads, clay lanes, sections of the Confederation Trail, and quiet country paved roads. 

This tour features nearly all of PEI's scenic Heritage roads, which are narrow red clay lanes preserved to look much like they did a century ago. Many are nicely shaded by a full canopy of trees. In addition, the queen stage passes through the hilliest part of the island, characterized by sharp climbs and steep descents on our famous red clay.

On the last day, there is an optional visits to Basin Head Beach, home of the white "singing sands".

Tour Duration
5 Days / 6 Nights

Accommodations
2- to 4-star hotels

Difficulty
Level 4

Distance
Daily Average = 108 km | 67 mi
Total = 540 km | 336 mi

Elevation
Daily Average = 866 m | 2,841 ft
Total = 4,329 m | 14,202 ft

Terrain
70% gravel, clay, trail
30% pavement

Starting from
$2,500 CAD per person
Book a Tour

Details & Itinerary

Day 1:  Charlottetown
Day 2:  North Cape - Mill River
Day 3:  Mill River - Summerside
Day 4:  Summerside - Charlottetown
Day 5:  Charlottetown - Brudenell
Day 6:  Brudenell - East Point
Charlottetown

Day 1

Settle into your hotel while we prep your bike for your 5 day, 540 km gravel adventure

Hotel

Charlottetown Inn & Conference Centre   ★★★

Centrally located downtown for easy access to restaurants and the Charlottetown waterfront.

  • Two Queen beds

  • Complimentary continental breakfast from 6-10am

  • Free WiFi

  • Indoor heated pool 

Things to Do

Schedule
Charlottetown
Day 1

10:30 AM - 4:00 PM

Pickup & Bike Prep

Once you reach Downtown Charlottetown, call us for pickup and we will transport you and your bike to Ted's Bicycle Studio to unpack and prep your bike (if required). If you are renting a gravel bike from us, we will set it up for you (ie. install your pedals, adjust saddle height). We will store your bike at the shop overnight and then drop you off Downtown.

4:00 PM

Check-in to Charlottetown Inn & Conference Centre

Spend your free time exploring Charlottetown's beautiful waterfront.

Fuel up for your 5-day ride at one of the many excellent restaurants nearby. Check out the list of partnering restaurants offering discounts to guests.
North Cape - Mill River

Day 2

Ride Details

Distance:   80 km  |  50 mi
Elevation:  363 m  |  1,191 ft
Terrain:      85% gravel

Difficulty:  🔥🔥🔥🔥

The route starts at North Cape, the northwesternmost point of PEI. There, your ride begins among the wind turbines and meanders around the cape on top of the rusty red cliffs. On the way to Mill River, you'll see fishing villages, sand dunes, lighthouses, farms, woodlands, and you'll ride sections of the Confederation Trail starting with Kilometer Zero in Tignish.

Points of Interest:

  • North Cape- home of the North Cape Wind Farm

  • Tignish run- ride along sand dunes to the busy fishing community

  • Tignish - start of the award-winning Confederation Trail  

  • Alberton - Stone Station Park features one of only two granite "boulder rail stations" in PEI

  • Northport - fishing community, gateway to the Sandhills

  • Elmsdale - farming community

Hotel

Mill River Resort   ★★★★

Tranquil setting by the Mill River on a 350-acre property

  • Two Queen beds

  • Onsite restaurant & bar

  • Indoor pool, water slide, and hot tub

  • Nature trails

  • Free WiFi

Schedule
East Point to Mill River
Day 2

6:00 AM - 8:00 AM

Breakfast

Enjoy a complimentary breakfast at the Charlottetown Inn & Conference Centre

8:30 AM - 9:00 AM

Pick-Up

Our shuttle vehicle will pick you up at the Charlottetown Inn. Your bike will already be loaded and ready to go.

9:00 AM - 11:15

Transport

Our shuttle vehicle will will transport you, your bike, and luggage from Charlottetown to North Cape. We'll stop at a bakery half-way for coffee and pastries.

11:30 AM

Lunch

Enjoy a tasty lunch while you take in the views at North Cape.

12:15 PM

Ride Segment 1

Ride 48.6 km from North Cape to Northport. The route passes through fishing communities and farmland. It is relatively flat and consists of red gravel and clay roads, sections of the Confederation Trrail and minimal pavement.

2:00 PM

Nutrition Break

Our support vehicle will meet you at the 48 km mark at the Northport beach. Snacks and water will be provided.

2:30 PM

Ride Segment 2

Ride 31.4 km from Northport to Mill River. The route passes through farming communities and consists of red gravel roads the Confederation Trail, and some pavement.

4:00 PM

Hotel

Your hotel for the night is the Mill River Resort. Check-in starts at 3pm. Get cleaned up before enjoying a delicious supper at the Callaghan's Restaurant and Bar, located onsite. Finish up your day with a stroll on the nature trails, or a swim in the indoor pool.

Don't worry about your bike. It will be washed ahead of tomorrow's ride.
Mill River - Summerside

Day 3

Ride Details

Distance:   111 km  |  69 mi
Elevation:  344 m  |  1,130 ft
Terrain:      60% gravel

Difficulty:  🔥🔥🔥🔥

Enjoy a warm-up on the Confederation Trail before hiting some backwoods gravel that takes you to Evangeline, home of the largest Acadian community in PEI. There you'll see fishing villages, and oceanviews, and peaceful farmland. Cool down as you enter Summerside riding along the waterfront.

Points of Interest:

  • O'Leary - home of the Canadian Potato Museum and the world's largest potato sculpture

  • Abram-Village - famous for its Acadian Festival during late August and early September

  • Cap Egmont - ocean views, fishing wharfs, lighthouse

  • Summerside - Canada's smallest city; home to a beautiful waterfront; don't miss Spinnaker's Landing, a market on the water featuring shops, decks, and boardwalks  

Hotel

Days Inn & Suites by Wyndham, Summerside   ★★

Located downtown for easy access to restaurants and the waterfront

  • Two Queen beds

  • Complimentary breakfast

  • Onsite guest laundry

  • Free WiFi

Schedule
Mill River to Summerside
Day 3

7:00 AM - 8:30 AM

Breakfast

Enjoy breakfast at the Mill River Resort onsite restaurant

9:00 AM

Ride Segment 1

Ride 56.5 km from Mill River to Saint Hubert. The route passes through farming and fishing communities. It is relatively flat and consists of red gravel and clay roads, sections of the Confederation Trrail and minimal pavement.

11:30 AM

Lunch

Enjoy a tasty lunch in Saint Hubert.

12:00 PM

Ride Segment 2

Ride 54.3 km from Saint Hubert to Summerside. The route passes through the Evangeline Region, home to the largest Acadian community in PEI. You'll see fishing communities, farmland, oceanviews, and lighthouses. It is relatively flat and consists of red gravel roads, sections of the Confederation Trrail and some pavement.

2:00 PM

Arrive in Summerside

Enjoy the waterfront views as you ride into Summerside. Head down to Spinnaker's Landing to enjoy some local ice cream before check-in.

3:00 PM

Hotel

Your hotel for the night is the Days Inn & Suites by Wyndham, Summerside. Check-in starts at 3pm. Get cleaned up before enjoying a delicious supper on the Summerside waterfront.

Don't worry about your bike. It will be washed ahead of tomorrow's ride.
Photo By Amy Hall
Summerside - Charlottetown

Day 4

Ride Details

Distance:   133 km  |  83 mi
Elevation:  1,950 m  |  6,398 ft
Terrain:      50% gravel

Difficulty:  🔥🔥🔥🔥

The queen stage starts with a warm up on the Confederation Trail and heads up to Darnley for some beautiful water views. Hop on a couple of PEI's scenic Heritage Roads before dropping down to Brookvale—the hilliest part of the Island, characterized by sharp climbs and steep descents on our famous red clay. Gravel tires 42mm or wider are advantageous on this route. Sections of this route were highlighted in our 2024 Red Hot Hilly Chili Graveler.

Points of Interest:

  • County Line Road - a red clay Heritage Road featuring a very high, rugged hill that provides spectacular views of the Gulf of St. Lawrence to the north and rolling hills to the south.

  • Millman Road - one of the first scenic Heritage Roads to be designated; features a large hill at the northern end that provides a beautiful view of the surrounding countryside.

  • New London - this route passes by the birthplace of Lucy Maud Montgomery, author of Anne of Green Gables

  • Mark Arendz Provincial Park at Brookvale - mountain bike destination known for its fast, flowy red dirt singletrack

  • Junction Road - Heritage Road featuring 100-year old trees, Lady's Slippers, and a place known as "Spooky Hallow"

  • McKenna, Appin, and Currie Roads - a winding and hilly network of red clay Heritage Road; greenery extends from hedgerow to a full canopy of trees that provides a refreshing shade

  • Victoria Park - enjoy riding beside the water in Charlottetown's largest waterfront park 

Hotel

Charlottetown Inn & Conference Centre   ★★★

Centrally located downtown for easy access to restaurants and the Charlottetown waterfront.

  • Two Queen beds

  • Complimentary continental breakfast from 6-10am

  • Free WiFi

  • Indoor heated pool 

Schedule
Summerside to charlottetown
Day 4

7:00 AM - 8:30 AM

Breakfast

Enjoy a complimentary breakfast at the Summerside Days Inn

9:00 AM

Ride Segment 1

Ride 46 km from Summerside to New London. The route starts off on the flat Confederation Trail before heading North to Darnley and some hilly red clay Heritage Roads.

11:00 AM

Nutrition Break

Enjoy a tasty snack in New London.

11:30 AM

Ride Segment 2

Ride 30 km from New London to Brookvale on red gravel and clay roads, and some pavement.

1:00 PM

Lunch

Enjoy a tasty lunch in Brookvale.

1:30 PM

Ride Segment 3

Ride 55 km from Brookvale to Charlottetown. The Brookvale region features hilly red clay Heritage roads before moving on to more pavement for the ride into Charlottetown.

4:00 PM

Hotel

Your hotel for the night is the Charlottetown Inn & Conference Centre. Check-in starts at 4pm. If you arrive early, grab some ice cream on your way through Victoria Park. Then get cleaned up before enjoying a delicious supper in Downtown Charlottetown.

Don't worry about your bike. It will be washed ahead of tomorrow's ride.
Photo By Shannon Burt
Charlottetown - Brudenell

Day 5

Ride Details

Distance:   118 km  |  73mi
Elevation:  1,009 m  |  3,310 ft
Terrain:      80% gravel

Difficulty:  🔥🔥🔥🔥

Ride out of town on the crushed gravel trails of Fullerton's Park before tackling the rolling red gravel and clay roads of the Dromore area. Enjoy a break by the freshwater "Spirit Spring" on Dromore Road before turning south to sample two rolling Heritage roads: Klondyke Road, and County Line Road. Preserved to look much as they did 100 years ago, these Heritage Roads are narrow red clay lanes under a delightful hardwood canopy. 

Points of Interest:

  • Fullerton's Creek Conservation Park - 140-acre conservation area in the Town of Stratford featuring crushed gravel trails and a viewing platform overlooking Fullerton's Marsh

  • Dromore Woodland Trails - a nature preserve with hiking trails that form part of the International Appalachian Trail.

  • Jack Campbell Road - narrow clay lane with a fast descent and sharp climb; bisects Dromore Woodlands park

  • Vanco Tulip Farms on Dromore - large tulip farm on Dromore Road just past Jack Campbell Road; tulips normally bloom in PEI between early May and mid June.

  •  Klondyke Road- a Heritage Road that cuts a swath through a border of sugar maple, birch, and spruce; once used by rumrunners in 1920s and 1930s to hide their contraband.

  • County Line Road - a Heritage Road located on the boundary of Queen's and Kings counties; horse-drawn carriages transported passengers along this lane in earlier years.  

Hotel

Rodd Brudenell River Resort   ★★★★

Tranquil setting within Brudenell River Provincial Park 

  • Two Queen beds

  • Three onsite dining options available 

  • Indoor & outdoor pool, sauna, hot tub

  • Free WiFi 

Schedule
charlottetown to Brudenell
Day 5

6:00 AM - 8:30 AM

Breakfast

Enjoy a complimentary breakfast at the Charlottetown Inn & Conference Centre

9:00 AM

Ride Segment 1

Ride 58 km from Charlottetown to Orwell. The route heads out of town on flat crushed gravel trails before tackling the rolling red gravel and clay roads of the Dromore region.

11:30 AM

Lunch Break

Enjoy a tasty lunch at the Sir Andrew MacPhail Homestead in Orwell.

12:00 PM

Ride Segment 2

Ride 60 km from Orwell to Brudenell on red gravel and clay roads, and some pavement. You'll hit three Heritage roads on this segment.

3:00 PM

Hotel

Your hotel for the night is the Rodd Brudenell River Resort. Check-in starts at 3pm. If you arrive early, its a short spin down to Georgetown, a charming fishing community full of historic heritage buildings. Then get cleaned up before enjoying a delicious supper at one of the three onsite restaurants.

Don't worry about your bike. It will be washed ahead of tomorrow's ride.
Brudenell - East Point

Day 6

Ride Details

Distance:   98 km  |  73 mi
Elevation:  663 m  |  2,175 ft
Terrain:      50% gravel

Difficulty:  🔥🔥🔥🔥

Ride toward East Point on mellow gravel roads, narrow canopied clay roads, and quiet country pavement. Enjoy views of sand dunes, lighthouses and fishing villages. Stop at the Elmira Station, which marks the end of the Confederation Trail, and then East Point, the easternmost tip of the Island. Enjoy a lunch break by the ocean in beautiful Souris. Finish off your day with a swim in the ocean at Basin Head Provincial Park, home of the "Singing Sands".

Points of Interest:

  • Souris - a seaside town hosting an interprovincial ferry terminal for service to Quebec's Magdalen Islands.   

  • North Lake - ride along the sand dunes to the North Lake Harbour, home of a busy fishing industry

  • Elmira Station - served as the end of the line for Prince Edward Island's railway for many years; now marks the end of the Confederation Trail

  • East Point - the easternmost point of PEI

  • Basin Head Provincial Park - features a pristine white sandy beach nicknamed the "singing sands" due to the squeaking sound the sand makes as you walk on it.

Hotel

Charlottetown Inn & Conference Centre   ★★★

Centrally located downtown for easy access to restaurants and the Charlottetown waterfront.

  • Two Queen beds

  • Complimentary continental breakfast from 6-10am

  • Free WiFi

  • Indoor heated pool 

Schedule
Brudenell - East Point
Day 6

7:00 AM - 8:30 AM

Breakfast

Enjoy breakfast at one of the onsite restaurants at the Brudenell River Resort

9:00 AM

Ride Segment 1

Ride 52 km from Brudenell to Souris. The route is a combination of rail trail, gravel, and pavement.

11:00 AM

Nutrition Break

Enjoy a tasty snack at the seaside Breakwater Park in Souris.

11:30 PM

Ride Segment 2

Ride 46 km from Souris to East Point on red gravel and clay roads, rail trail, and some pavement. You'll hit two Heritage Roads on this segment and ride to the end of the Confederation Trail in Elmira.

1:30 PM

Lunch

Enjoy a delicious lunch at East Point

2:00 PM

Transport to Basin Head

Hop in the van for a quick drive to nearby Basin Head Provincial Park where you can dip your toes in the soft "singing sands" that squeak as you walk, and swim in the ocean if you wish. Showers and a concession stand are available.

4:00 PM

Transport to Charlottetown

Our shuttle van will transport you back to Charlottetown where your hotel for the night is the Charlottetown Inn & Conference Centre. 

Don't worry about your bike. It will be washed, boxed up if you are flying, and delivered back to the hotel.
Book a Tour

Tailwind Cycling Tours
41 Hollis Ave. Unit 41, Stratford PE, C1B 4A1

902-367-5191

info@tailwindcyclingtours.ca